i think it's possible that a small group of pirate fans built this moc together especially for this event, whatever event it may be...

It's definitely one of the 1000steine events they have every summer in Berlin. It's called "1000steine-Land". If I'm deciphering the display cards correctly and "cross-check" with these pictures it should be from 2003...

The story I was told he went the opposite direction to see if it was faster to get to India... Have I been lead astray here?

i'm afraid so.
Columbus went to the opposite direction because the Portugese were in control of the searoutes to India (via the Cape) and the moslims controled the Suez, so it was practically impossible for Spain to get ships to India via the traditional ways. Colombus, an italian, had no choice but to go the other way, hoping, he'd be able to reach India and China. In the end, they were all after the same thing: luxury goods. however, the Portugese were mainly interested in organising trading posts, the Spaniards wanted to colonise areas all around the world...

Later on, once both nations had more or less maped the world, they made an agreement that would close the routes to the East for Spain, but she would get the americas as a compensation, except for Brasil.